Cinnamon sugar pillow cookies are soft and delightful holiday cookies, with a surprise cream cheese filling hidden inside!
Fluffy cinnamon sugar pillow cookies
These pillow soft cookies are like a cinnamon roll, a sugar cookie, and a cream cheese Danish all in one incredibly delicious cookie.
Each year around Christmas, they are always one of the first cookies to disappear on the holiday cookie tray, and for very good reason.
If you haven’t started baking cookies this holiday season, why not begin today?
One pillowy bite, and you will fall in love.
Also try these Vegan Chocolate Chip Cookies
The best pillow sugar cookies
Today’s recipe is an update of an incredibly popular sugar cookie recipe I first posted all the way back in 2012.
This new and improved version of the recipe is easier to follow and makes a bigger batch, because you will definitely want more of these cookies once you try them!
They are hands down the best stuffed sugar cookies you will ever taste.
The light and fluffy homemade cookies are always a big hit with both vegans and non vegans, and they are the perfect holiday cookie to give as a gift.
But if you do want to send them to others, I definitely recommend making extra so you can keep a few for yourself.
Use leftover cream cheese for this Oreo Fluff Recipe
Cinnamon sugar pillow cookie recipe video
Above, watch the step by step video
Ingredients for the recipe
The cookie base calls for flour, sugar, baking soda, baking powder, salt, oil or butter, water, and pure vanilla extract.
You will need equal parts ground cinnamon and sugar for the optional coating. The cheesecake filling ingredients are simply powdered sugar and cream cheese.
Flour – Spelt flour is my preference here. It is a healthy, whole grain alternative to white flour yet yields a lighter texture than whole wheat flour. All purpose flour, oat flour, and some brands of gluten free flour also work.
Sugar – This can be traditional white sugar, unrefined coconut sugar, or granulated xylitol for sugar free cookies. I have not tried pure maple syrup or honey so cannot recommend either of those options as substitutions.
Cream Cheese – Dairy cream cheese and nondairy cream cheese work equally well in these cookies. As a fun alternative, you can stuff the cookies with something entirely different, such as crunchy peanut butter or Homemade Nutella.
Butter – Look for salted or unsalted butter at the grocery store. For vegan pillow cookies, go with a full fat plant based alternative. Or substitute melted coconut oil or vegetable oil for crispier sugar cookies without butter.
Vanilla Extract – Buy pure vanilla extract for the best results. Imitation vanilla flavor is less expensive but will impart an artificial aftertaste that you do not want.
How to make the cookies
Start by gathering all of your base and filling ingredients.
For the optional filling: Let the cream cheese come to room temperature so it will be easier to blend smoothly.
Add the powdered sugar to the softened cream cheese, and beat in a stand mixer or with hand beaters. If you do not own either of these, you can also patiently whip it together by hand until thick and smooth.
Set the filling aside while you make the sugar cookies.
For the cookies: Combine the flour, baking soda, baking powder, salt, and sugar in a large mixing bowl. Stir well, then add in the melted butter or oil, water, and vanilla extract to form a sugar cookie dough.
If the dough is too dry for some reason (climate, humidity, elevation, etc.), very slowly add a little more water or oil.
Use your hands to smush the cookie dough into one giant ball. Or use my less messy trick of transferring the mixture to a large Ziploc bag and smushing it into a ball from inside the bag.
Break off large cookie sized amounts, and roll into balls.
If filling the cookies, break each ball in half. Add about a half teaspoon of cream cheese filling to one half, then place the other piece of dough on top and roll back into a ball.
For soft, chewy cookies, chill the unbaked cookie dough balls for at least thirty minutes or until cold to the touch. You may skip this step if in a rush.
Preheat the oven to 325 degrees Fahrenheit.
Roll the balls in cinnamon sugar and place them on a cookie baking tray.
Bake on the center rack of the preheated oven for eleven minutes. The cookies should look underdone when you take them out of the oven.
Let cool before handling, during which time they will firm up considerably.
Pillow cookie storage tips
Once cooled, transfer cookies to a serving tray or container.
Store leftover cookies in an airtight container for up to five days on the counter. Or freeze leftovers in a covered container for up to about three months.
If you like soft pillow cookies, go with a plastic container. For chewy cookies with a slightly crispy texture, store them in a glass container.
Cinnamon Sugar Pillow Cookies
Ingredients
Pillow Cookies
- 1 1/2 cup flour (spelt, white, or oat)
- 3/4 tsp baking soda
- 1/2 tsp baking powder
- 1/2 tsp salt
- 1/2 cup sugar (or coconut sugar or xylitol)
- 6 tbsp oil or butter
- 1 1/2 tbsp milk of choice
- 1 tsp pure vanilla extract
Cream Cheese Filling (optional)
- 1/4 cup cream cheese or vegan cream cheese
- 1 1/2 tbsp powdered sugar or sugar free powdered sugar
- equal parts cinnamon and sugar or xylitol if desired for coating
Instructions
- In a mixing bowl, combine first five ingredients, and stir well. Stir in the oil, milk, and vanilla to form a cookie dough. Only add extra milk if it's still too dry after a full minute of stirring. (I've never had to add more than the 1 1/2 tbsp milk.) Smush into a giant ball with your hands, or transfer dough to a plastic bag and smush into a ball once the dough is inside the bag. Now roll into balls. Break balls in half, flatten each half a bit and add a little filling to one half, then place the other half on top and re-roll. For softer cookies, chill 30 minutes or up to a day. Preheat oven to 325 F. Roll balls in cinnamon sugar, place on a baking tray, and bake on the center rack 11 minutes. They'll look underdone when you take them out, so let them cool fully on the baking tray and they will firm up as they cool.View Nutrition Facts
Video
Notes
Reader Favorite Holiday Cookie Recipes
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I have several ideas.
A margerita cupcake! This one has a story. See, one time I was messing around with some weird ingrediants and had a (genius) idea (well, that and because I had just gone grocery store impulse shopping andbought a 5 pound bag of limes while Trader-Joe’s-Impulse-Shopping ;-D), so I mixed up some cupcake batter and went crazy with tequilla, lime, green melted sprinkles, and white crystal-y sugar decorations. Thus, margerita cupcakes were born, much to my enthusiasm. Anyways, I was thinking you could somehow make a cookie out of this and post it in the dead of winter, when everyone wants summer to just hurry up and arrive. Y’know, to give us hope 😀
Actually, now I am so preocupied with the idea of a margerita cookie, I cant remember what my other ideas were. Hmmmm…;-)
And happy cookie season! 😀
Wait. I take back my previous statement of not knowing any other ideas.
French merangues!
I have no clue how these would be possible to vegan-ify, considering that they are basically just really, really fluffy eg whites whipped up and baked into cookies. But before I became a vegan really recently (I had been a vegetarian with dairy before that for about 7 years), these cookies were my favorites. So crispy and fluffy and light and melt-in-your-mouth-delicious! And I know that if anyone could make these babies, it would be you, CCK! 🙂
I’d love to see a sushi cookie! Coconut as the rice, chocolate as the seaweed… Funky and yummy!
I like the idea of Starbucks-inspired cookies, especially the Earl Grey latte one! Pumpkin spice latte cookies?
Also, I had some really good fig butter from Trader Joe’s today with some dark chocolate melted in my oatmeal. That might make a yummy cookie.
These look FANTASTIC! Love the cream cheese surprise inside! As far as interesting flavor combos for Christmas cookies, I always think the Luna Cafe blog has the craziest and yummiest cookie flavor combos! Here’s the link, just scroll down to “Cookies”:
http://thelunacafe.com/recipes/recipes-by-category-2/
I just made the cookies they’re so amazing. I tried to double to recipe but it ended up making the same amount I have no idea how I did that. I had to add more oil and milk than in the recipe my dough turned out very dry for some reason. And next time I’m gonna need to make more filling. But overall these cookies are so delicious. I’m definitely making them again!
These looks so soft and ooey gooey! Yum! How about some sort of goji berry/pistachio cookie? It would be delicious and beautiful, I bet!
Hi there- I was wondering how to stuff the cookies? I have to idea how to put the filling in! Thanks!
Just put a little inside each cookie, with a spoon.
katie can you invent a christmas cookie useing flavor like maybe some raw ginger , molases or marzipan i think that would be great or even doing the standard decorating sugar cookies would be an awesome vegan recipe
Hi Katie–I just love your website and I enjoy seeing all the recipes you share. Thank you so much!
You asked about cookie ingredients—-have you ever heard or tasted Rumchatta? It is a liquoer that tastes like cinnamon toast crunch milk–it’s delicious. They have a cupcake recipe out there–but since you are so creative I wondered if you could come up with a cookie recipe for it.
Would love to try one if you come up with it and I know it could be a hit.
If you try one–please let me know!
thanks and happy cookie baking and happy holidays!
Theresa
I will have to look for it!
Oh, these are definitely getting made in my kitchen!
Hey Katie,
I tried this and it looks like powder, not even mealy enough to be compared to a pie crust and barely even a crumble topping. This needs much more liquid. Did you mean tsp of milk or cups or tbsp? Something’s missing…..
thanks in advance,
jackie
It doesn’t need more liquid. I’ve made them twice and both times came out perfect.
Smitten Kitchen’s new cookbook has a recipe for buttered popcorn cookies…
Would it work to stuff the cookies with something like a piece of chocolate?
very very crumbly, needs more milk and oil, also 3/4 cup of ww flour is 90g and not 120, so my dough was doubly crumbly for the extra flour 🙁
The recipe doesn’t call for whole wheat flour.
Yummy. This is my new favorite cookie!
Next I want to try stuffing it with chocolate. 🙂